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Josephine is a perfect example of a bad girl gone worse. She had been paddled spanked, paddled, and caned, but for some reason her attitude and behavior never seemed to change. This is when the headmaster had enough, and now felt it was time to place her

Josephine is a perfect ex..

Shelia is a girly maid who loves to wear a pink apron while she cleans the headmasters house. The headmaster has told Shelia he hates the color pink and decides to punish her for disobeying him. He grabs her by the arm, throws her over his knee and proce

Shelia is a girly maid wh..

In todays Caning video, we see what happens when Angel really crosses the line. Angel had been caught sneaking back and forth between the boys and girls school, selling her body to the over eager boy students. When the Headmaster caught wind of this, he

In todays caning video, w..

Mischevious Xenia recieves corporal punishment from the headmaster

Mischevious xenia recieve..

The headmaster heard Julie was smoking in the girls bathroom, and wanted to put an end to the nasty habit. He had her brought into his den, and immediately instructed her to bend over and prepare to receive her punishment. She reluctantly obliged, kn

The headmaster heard juli..

Sexy little Lexi is sent away by her headmaster for a transatlantic education she won't forget. Across the pond she encounters likeminded bad girls who happily lead her astray. Before she knows it she's receiving a hardcore lesson in sucking and fucking. George Uhl Jazz Duro Mackenzee Pierce

Sexy little lexi is sent..

Nicky has disobeyed her teachers yet again and is called in to the headmasters office for punishment. The headmaster orders Nicky to remove her skirt and panties and bend over the desk. He then uses his cane pummel her behind as she cries out in a mix o

Nicky has disobeyed her t..

Tiffany was placed on our rudimentary rack, hands and feet chained. She had always dressed slutty, with her tits spilling out of her tops and barely covered legs. The headmaster knew this and wanted to teach her a lesson. He felt he should torture her

Tiffany was placed on our..

Most of the girls at the school had enough decency and respect to not over emphasize there feminine features. Halli however was quite the opposite. She was always wearing overly tight tops, showing off her full breast. This is when the headmaster felt h

Most of the girls at the..

Sara has failed to clean her room and is dragged to the couch to receive her OTK spanking. Sara kicks and screams as the headmaster throws her over his lap and gives her the spanking she deserves. He lifts up her skirt and begins to turn her ass a rosy

Sara has failed to clean..

Miss Heron has been called to the headmasters office for wearing high heels, yet again. She kicks her high heels in the air as she receives her ATK spanking. The headmaster delivers some blows using his firm hand over her skirt before lifting it up to r

Miss heron has been calle..

Sexy little Lexi is sent away by her headmaster for a transatlantic education she won't forget. Across the pond she encounters likeminded bad girls who happily lead her astray. Before she knows it she's receiving a hardcore lesson in sucking and fucking. George Uhl Jazz Duro Mackenzee Pierce

Sexy little lexi is sent..

Katty has been extra naughty this week and is taught a stern lesson is this sexy caning video. The headmaster wakes her up, bends her over the bend and proceeds to give her a good caning. After a few spankings with his cane, the headmaster lowers Kattys

Katty has been extra naug..

Katty has recently dyed her hair, something the school forbids. The headmaster gets word of this, calls Katty to his office and pulls her over his lap to administer her punishment. He lifts up her skirt, lowers her panties and gives her an OTK spanking

Katty has recently dyed h..

The headmaster has just received Angelas failing report card and decides to teach her a valuable lesson. He drags over a chair, pulls her across his lap, and gives her a good old-fashioned OTK spanking. He then removes her panties and uses his firm hand

The headmaster has just r..

Xenia and Lolita are caught cheating on their geography exam and receive a proper spanking. The headmaster takes turns giving both Xenia and Lolita a firm OTK spanking. Each of them kick their legs and cry out in a mix of pleasure and pain as their white

Xenia and lolita are caug..

Dzejisis has been extra naughty and is placed in a guillotine to receive her caning. The headmaster lifts her dress and uses his cane to turn her bare bottom a lovely shade of pink. The caning is completed only when the headmaster decides her bottom is t

Dzejisis has been extra n..

Some girls need the stiff hand of a man to best learn their lesson, and thats what was needed for Lina. She had repeatedly disrespected her headmaster, and so it was time for him to ensure it would never happen again. He ensured her ass was as red as hi

Some girls need the stiff..

Naughty Paris forgot to clean the kitchen yet again and receives her punishment in this sexy spanking film. She unbuckles her belt and lowers her jeans, revealing her sexy white bottom. The headmaster grabs her, throws her over his knee and uses his fir

Naughty paris forgot to c..

Eva had been walking around school without panties flashing her fellow classmates. She saw this as a big joke, and a way to make her dull life all the more exciting. The headmaster however saw this and took immediate action. She was not to make a mocke

Eva had been walking arou..

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